9419. Tiamulin

Nomenclature

CAS number: 55297-95-5
(3aS,4R,5S,6S,8R,9R,9aR,10R)-[[2-(Diethylamino)ethyl]thio]acetic acid 6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester; 14-desoxy-14-[(2-diethylaminoethyl)mercaptoacetoxy]mutilin; thiamutilin; SQ-14055.
C28H47NO4S; mol wt 493.74.
C 68.11%, H 9.59%, N 2.84%, O 12.96%, S 6.49%.

Description and references

Derivative of pleuromutilin, q.v. Prepn: H. Egger, DE 2248237 corresp to US 3919290 (1973, 1975 both to Sandoz); H. Egger, H. Reinshagen, J. Antibiot. 29, 915 (1976). Biosynthesis: F. Knauseder, E. Brandl, ibid. 125. In vitro activity: H. Werner et al., ibid. 31, 756 (1978). Metabolism: J. Dreyfuss et al., ibid. 32, 496 (1979). Effect vs Mycoplasma: C. O. Baughn et al., Avian Dis. 22, 620 (1978); R. F. Goodwin, Vet. Rec. 104, 194 (1979). Mechanism of action: G. Hgenauer in Antibiotics vol. 5(pt. 1), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 344-360. Treatment of swine dysentery: M. D. Anderson, Vet. Med. Small Anim. Clin. 78, 98 (1983).

Chemical structure

Derivative

Fumarate.

Nomenclature

CAS number: 55297-96-6
81723 hfu; SQ-22947; Denagard (Novartis); Dynamutilin (Novartis); Tiamutin (Novartis).
C32H51NO8S; mol wt 609.81.
C 63.03%, H 8.43%, N 2.30%, O 20.99%, S 5.26%.

Properties

Crystals from acetone, mp 147-148° (after stirring in ethyl acetate and drying at 60° and 80° overnight).

Therapeutic Category (Veterinary)

Antibacterial.